The tocols are known to have beneficial health effects when provided as a dietary supplement. Efficient transport out of the liver is necessary for the tocols to deliver the beneficial health effects. The tocols are transported out of the liver and into the blood stream by a protein called αTTP (tocopherol transfer protein). Some tocols, specifically the tocopherols, are more efficiently transported out of the liver and into the blood stream than the tocotrienols and have a longer half-life in the body due to their higher binding affinity to αTTP than their tocotrienol counterparts.
The tocotrienols have recently been shown to have some beneficial health effects not seen with the tocopherols. However, their limited half-life in the body greatly reduces their bioavailability, and limits their usefulness. Provided herein are methods of making tocol derivatives with modifications to the hydrocarbon tail to allow more efficient binding and uptake of tocols with unsaturated hydrocarbon tails by αTTP. The derivatives were named tocoflexols to indicate the increased flexibility of the hydrocarbon tail as compared to the tails of tocotrienols and differentiate this class of compounds from the tocopherols and tocotrienols. Methods of making tocopherol and tocotrienol derivatives with one to three double bonds in the hydrocarbon tail are described herein.